Senior Director, Strategy & Execution

Ensono

7h•$205,000 - $278,000•Hybrid

About The Position

At Ensono, our Purpose is to be a relentless ally, disrupting the status quo and unleashing our clients to Do Great Things! We enable our clients to achieve key business outcomes that reshape how our world runs. As an expert technology adviser and managed service provider with cross-platform certifications, Ensono empowers our clients to keep up with continuous change and embrace innovation. We can Do Great Things because we have great Associates. The Ensono Core Values unify our diverse talents and are woven into how we do business. These five traits are the key to achieving our purpose: Honesty, Reliability, Curiosity, Collaboration, and Passion. Ensono’s Strategy team sets the company’s annual strategy, turns it into a governed portfolio of strategic initiatives, focuses corporate development, and runs the executive forums that keep the CEO, the executive leadership team (ELT) and the board focused on what matters most. This role sits at the center of how Ensono sets and executes strategy, with regular exposure to the CEO, President, executive team, board and investors. It is designed as a path to broader strategy leadership, with growing ownership of the strategy cycle, corporate development and executive forums over time. We are looking for a senior strategy leader who can both help shape the strategy and drive execution. You will own the machinery that translates strategy into action, lead critical initiatives personally, influence executive decisions, and develop a broad understanding of every aspect of Ensono's business. This is not a project management or governance role. Program discipline is table stakes; the job requires judgment, business acumen and original thinking. You will spot the initiative that is drifting before it misses, write the memo that frames the decision and, from a vantage point close to every part of the business and its leaders, genuinely shape Ensono’s strategy with ideas of your own. This role is ideal for a highly strategic, intellectually curious leader who wants to influence the direction of a growing company while building the experience required for future executive-level strategy leadership positions.

Requirements

10 or more years in corporate strategy, strategy operations, consulting, corporate development or a chief-of-staff role, including 3 or more working directly with C-suite executives.
A track record of running an enterprise planning or strategic initiative process across multiple functions, including portfolio governance, decision gates and executive readouts.
Evidence of original strategic thinking: ideas you originated that changed a company’s direction, offerings or operating model.
Strong structured problem solving and financial fluency: business cases, P&L and EBITDA impact, contract economics and investment theses.
Executive-grade communication, from a six-page narrative memo to a one-slide board summary.
The ability to lead without authority and hold senior leaders accountable, often people more senior than you.
The presence to sit in senior leaders’ staff meetings as both listener and contributor, and the judgment to know what to share and what stays in the room.
Rigorous program management habits (charters, plans, risk logs, status reporting) used as a means rather than the end.
Hands-on fluency with AI productivity tools, data and dashboards.
Absolute discretion with confidential information, including transactions, board matters and personnel.
A bachelor’s degree.
10% travel requirement, primarily for executive strategy sessions, advisory council meetings, client engagements and acquisition diligence

Nice To Haves

An MBA or equivalent graduate degree.
Experience in IT or managed services, mainframe or hybrid cloud, or enterprise B2B technology.
Hands-on M&A, joint venture or partnership experience, including diligence and integration.
Experience in a private equity-backed company, including board and investor reporting.
Experience running a customer advisory board or executive client program.

Responsibilities

Shape the strategy from close to the business: Sit in on executive leaders’ staff meetings to stay close to the business and to give as well as take, keeping leaders current on company priorities and what is moving elsewhere in Ensono. Connect the dots across functions, spot emerging risks and opportunities early, and bring them to the CSO, CEO and President with a clear point of view. Contribute original ideas to the strategy, from new offerings and market moves to operating-model changes, and turn the strongest into strategy memos and initiative proposals. Help the CEO and President do their jobs better by anticipating what they need and turning what is happening across the business into content for the ELT and the board.
Run the annual strategy cycle and initiative portfolio: Own the annual strategy process end to end, from theme intake and charters to strategy memos, decision gates and the executive strategy session, improving it each cycle. Stand up each approved initiative with a charter, sponsor, accountable lead, plan and measures of success, and hold the portfolio to account through the ELT, senior leadership team, monthly business review and board rhythm. Surface risks, dependencies and decisions early, and escalate with a clear recommendation rather than a status update. Coach initiative leads on problem structuring, root-cause analysis and decision-ready writing, and maintain the templates and toolkit that make good submissions easy. Personally lead one or two of the high-priority initiatives or special projects each year.
Drive the executive operating rhythm: Coordinate and run the monthly business review: shape the agenda with the CEO and President, work with each leader on their content, hold the quality bar on what is presented, and follow through on the decisions and actions that come out of it. Run the other forums the Strategy team owns, including the weekly AI program standup, initiative readouts and critical-issue tracking for the CEO. Prepare and pressure-test materials for the ELT, the board and its committees, and our private equity sponsor, including directly helping produce the CEO’s board content. Track decisions and actions to closure, and turn meetings into crisp summaries that people act on.
Lead corporate development and strategic analysis: Help identify where acquisitions, joint ventures or partnerships are the right path and, when one is chosen, source and screen options and support diligence and integration. Evaluate and shape joint ventures and partnerships, including client-anchored models: frame the rationale for every party, build the business case and prepare partner discussions. Scope and manage external advisers and specialists, from statement of work through final readouts. Lead market and competitive intelligence, including competitor results, market studies and the impact of AI on our markets, and translate it into implications for leadership.
Steward executive client and market programs: Co-lead the Executive Advisory Council, Ensono’s forum of client executives: member recruitment and onboarding, agenda design, meeting delivery, and synthesis of what members tell us. Connect advisory council and voice-of-the-client insight to the strategy process and to initiative priorities.
Shape transformation and build the strategy office: Help shape operating-model changes, such as governance and intake for a proposed enterprise PMO, and own other transformation programs as assigned. Build an AI-enabled strategy office: dashboards, agents and automated summaries that reduce manual coordination and give leaders answers without having to ask. Represent the Strategy team across the executive and senior leadership teams, and deputize for the SVP and CSO in forums as needed.

Benefits

Unlimited Paid Days Off
Three health plan options
401k with company match
Eligibility for dental, vision, short and long-term disability, life and AD&D coverage, and flexible spending accounts
Family Forming Benefit including fertility coverage and adoption/surrogacy reimbursement
Paid childbearing and paternal leave
Education Reimbursement, Student Loan Assistance or 529 College Funding
Sabbatical leave
Wellness program
Flexible work schedule